DE69011677D1 - METHOD FOR PRODUCING SUBSTITUTED ETHENES. - Google Patents
METHOD FOR PRODUCING SUBSTITUTED ETHENES.Info
- Publication number
- DE69011677D1 DE69011677D1 DE69011677T DE69011677T DE69011677D1 DE 69011677 D1 DE69011677 D1 DE 69011677D1 DE 69011677 T DE69011677 T DE 69011677T DE 69011677 T DE69011677 T DE 69011677T DE 69011677 D1 DE69011677 D1 DE 69011677D1
- Authority
- DE
- Germany
- Prior art keywords
- pct
- arylalkyl
- alkylamines
- nitrodithio
- sec
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 150000003973 alkyl amines Chemical class 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 abstract 1
- ULOTWPOKIYOEQN-UHFFFAOYSA-N 2-nitroethanedithioic acid Chemical compound [O-][N+](=O)CC(S)=S ULOTWPOKIYOEQN-UHFFFAOYSA-N 0.000 abstract 1
- DXSUORGKJZADET-UHFFFAOYSA-N 3,3-dimethylbutan-2-amine Chemical compound CC(N)C(C)(C)C DXSUORGKJZADET-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000003975 aryl alkyl amines Chemical group 0.000 abstract 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 abstract 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 abstract 1
- -1 heterocyclic alkylamines Chemical group 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/27—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Underground Structures, Protecting, Testing And Restoring Foundations (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
PCT No. PCT/GB90/00501 Sec. 371 Date Jul. 18, 1991 Sec. 102(e) Date Jul. 18, 1991 PCT Filed Apr. 4, 1990 PCT Pub. No. WO90/12002 PCT Pub. Date Oct. 18, 1990.A potassium salt useful in the production of certain N-substituted alkyl or arylalkyl thionitroethenamines is produced by the reaction of the dipotassium salt of a 2-nitrodithio aliphatic acid such as 2-nitrodithio acetic acid with branched chain primary alkylamines, secondary alkylamines, arylalkylamines or heterocyclic alkylamines such as dimethylamine, pinacolylamine, benzylamine or piperonylamine, thereby converting one only of the KS-groups to an alkylamine group. The resulting monopotassium salt may be alkylated or arylalkylated to produce an N-substituted alkyl or arylalkyl thionitroethenamine. This compound may be reacted with a suitable amine to produce compounds containing the pharmaceutically active grouping -NHC(=CHNO2)NHX, wherein X represents an alkyl, arylalkyl or heterocyclic alkyl group.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898907700A GB8907700D0 (en) | 1989-04-05 | 1989-04-05 | Preparation of substituted ethenes |
| PCT/GB1990/000501 WO1990012002A1 (en) | 1989-04-05 | 1990-04-04 | Preparation of substituted ethenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69011677D1 true DE69011677D1 (en) | 1994-09-22 |
| DE69011677T2 DE69011677T2 (en) | 1995-02-09 |
Family
ID=10654520
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69011677T Expired - Fee Related DE69011677T2 (en) | 1989-04-05 | 1990-04-04 | METHOD FOR PRODUCING SUBSTITUTED ETHENES. |
| DE4010888A Expired - Lifetime DE4010888C2 (en) | 1989-04-05 | 1990-04-04 | Process for the preparation of a 1- (alkylamino) -2-nitroethenthiol potassium salt, process for the preparation of an N-substituted 1-alkylthio-2-nitroethenamine, process for the preparation of N- [2- [5- (dimethylamino) methyl-2 -furanylmethylthio] -ethyl] -N'-methyl-2-nitro-1,1-ethenediamine (ranitidine) and 1 - [[2 - [[[5 - [(dimethylamino) methyl] -2-furanyl] methyl ] -thio] -ethyl] -amino] -2-nitroethenthiol potassium salt |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4010888A Expired - Lifetime DE4010888C2 (en) | 1989-04-05 | 1990-04-04 | Process for the preparation of a 1- (alkylamino) -2-nitroethenthiol potassium salt, process for the preparation of an N-substituted 1-alkylthio-2-nitroethenamine, process for the preparation of N- [2- [5- (dimethylamino) methyl-2 -furanylmethylthio] -ethyl] -N'-methyl-2-nitro-1,1-ethenediamine (ranitidine) and 1 - [[2 - [[[5 - [(dimethylamino) methyl] -2-furanyl] methyl ] -thio] -ethyl] -amino] -2-nitroethenthiol potassium salt |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US5371247A (en) |
| EP (1) | EP0466733B1 (en) |
| JP (2) | JP2954270B2 (en) |
| KR (2) | KR920701140A (en) |
| AT (2) | AT400030B (en) |
| BE (1) | BE1003124A5 (en) |
| CA (2) | CA2013841C (en) |
| CH (1) | CH681008A5 (en) |
| DE (2) | DE69011677T2 (en) |
| DK (2) | DK84390A (en) |
| ES (2) | ES2019246A6 (en) |
| FI (2) | FI110939B (en) |
| FR (1) | FR2645535B1 (en) |
| GB (2) | GB8907700D0 (en) |
| GR (1) | GR1001302B (en) |
| HU (3) | HU9203905D0 (en) |
| IE (2) | IE61894B1 (en) |
| IL (1) | IL94002A (en) |
| IN (3) | IN170319B (en) |
| IT (1) | IT1242481B (en) |
| NL (1) | NL194699C (en) |
| PT (1) | PT93659B (en) |
| SE (1) | SE509459C2 (en) |
| WO (1) | WO1990012002A1 (en) |
| ZA (1) | ZA902592B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8907700D0 (en) * | 1989-04-05 | 1989-05-17 | Fine Organics Ltd | Preparation of substituted ethenes |
| PT101031B (en) * | 1991-11-05 | 2002-07-31 | Transkaryotic Therapies Inc | PROCESS FOR THE SUPPLY OF PROTEINS BY GENETIC THERAPY |
| US5686588A (en) * | 1995-08-16 | 1997-11-11 | Yoo; Seo Hong | Amine acid salt compounds and process for the production thereof |
| AU2001264174A1 (en) | 2000-04-21 | 2001-11-07 | Ioannis Pallikaris | Device for the shaping of a substance on the surface of a cornea |
| CN104119257B (en) * | 2013-04-26 | 2016-08-03 | 石家庄康坦福化工科技有限公司 | A kind of preparation method of 1-methylamino-1-methyl mercapto-2-nitroethylene |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1554153A (en) * | 1975-05-15 | 1979-10-17 | Smith Kline French Lab | Process for making 2-amino-2-alkylthionitroethylenes |
| IT1168163B (en) * | 1981-08-18 | 1987-05-20 | Ausonia Farma Srl | COMPOUND WITH ANTI-ULTER ACTIVITY, PROCEDURE FOR ITS PREPARATION AND RELATIVE PHARMACEUTICAL COMPOSITIONS |
| PT76557B (en) * | 1982-04-16 | 1986-01-21 | Inke Sa | Process for preparing furan derivatives and addition salts thereof and of pharmaceutical compositions containing the same |
| ES8500618A1 (en) * | 1983-06-21 | 1984-11-16 | Union Quimico Farma | Prepn. of methylamino methylthio nitro-ethene |
| GB8415254D0 (en) * | 1984-06-15 | 1984-07-18 | Glaxo Group Ltd | Amine derivatives |
| ES2003781A6 (en) * | 1987-02-06 | 1988-11-16 | Unio Quimico Farmaceutica S A | N-methyl 1-methylthio 2-nitro ethenamine prepn. |
| GB8907700D0 (en) * | 1989-04-05 | 1989-05-17 | Fine Organics Ltd | Preparation of substituted ethenes |
-
1989
- 1989-04-05 GB GB898907700A patent/GB8907700D0/en active Pending
- 1989-04-05 HU HU9203905A patent/HU9203905D0/en unknown
-
1990
- 1990-04-04 KR KR1019910700948A patent/KR920701140A/en not_active Application Discontinuation
- 1990-04-04 US US07/730,963 patent/US5371247A/en not_active Expired - Fee Related
- 1990-04-04 ZA ZA902592A patent/ZA902592B/en unknown
- 1990-04-04 BE BE9000381A patent/BE1003124A5/en not_active IP Right Cessation
- 1990-04-04 IN IN247/MAS/90A patent/IN170319B/en unknown
- 1990-04-04 CH CH1132/90A patent/CH681008A5/fr not_active IP Right Cessation
- 1990-04-04 ES ES9000971A patent/ES2019246A6/en not_active Expired - Fee Related
- 1990-04-04 WO PCT/GB1990/000501 patent/WO1990012002A1/en active IP Right Grant
- 1990-04-04 AT AT0080090A patent/AT400030B/en not_active IP Right Cessation
- 1990-04-04 JP JP2090034A patent/JP2954270B2/en not_active Expired - Lifetime
- 1990-04-04 GB GB9007568A patent/GB2230526B/en not_active Expired - Lifetime
- 1990-04-04 JP JP2505189A patent/JP3003946B2/en not_active Expired - Fee Related
- 1990-04-04 IL IL9400290A patent/IL94002A/en not_active IP Right Cessation
- 1990-04-04 DE DE69011677T patent/DE69011677T2/en not_active Expired - Fee Related
- 1990-04-04 CA CA002013841A patent/CA2013841C/en not_active Expired - Lifetime
- 1990-04-04 US US07/503,987 patent/US5112995A/en not_active Expired - Lifetime
- 1990-04-04 DK DK084390A patent/DK84390A/en not_active Application Discontinuation
- 1990-04-04 HU HU902080A patent/HU207991B/en unknown
- 1990-04-04 KR KR1019900004645A patent/KR0147820B1/en not_active IP Right Cessation
- 1990-04-04 GR GR900100250A patent/GR1001302B/en not_active IP Right Cessation
- 1990-04-04 SE SE9001236A patent/SE509459C2/en not_active IP Right Cessation
- 1990-04-04 FR FR909004313A patent/FR2645535B1/en not_active Expired - Lifetime
- 1990-04-04 HU HU902945A patent/HUT58285A/en unknown
- 1990-04-04 DE DE4010888A patent/DE4010888C2/en not_active Expired - Lifetime
- 1990-04-04 DK DK90905245.8T patent/DK0466733T3/en active
- 1990-04-04 ES ES90905245T patent/ES2057549T3/en not_active Expired - Lifetime
- 1990-04-04 AT AT90905245T patent/ATE110055T1/en not_active IP Right Cessation
- 1990-04-04 IT IT04782990A patent/IT1242481B/en active IP Right Grant
- 1990-04-04 IE IE122290A patent/IE61894B1/en not_active IP Right Cessation
- 1990-04-04 PT PT93659A patent/PT93659B/en not_active IP Right Cessation
- 1990-04-04 CA CA002046293A patent/CA2046293C/en not_active Expired - Fee Related
- 1990-04-04 EP EP90905245A patent/EP0466733B1/en not_active Expired - Lifetime
- 1990-04-04 IE IE122190A patent/IE65395B1/en not_active IP Right Cessation
- 1990-04-04 NL NL9000790A patent/NL194699C/en not_active IP Right Cessation
- 1990-04-04 FI FI901696A patent/FI110939B/en active IP Right Grant
-
1991
- 1991-10-04 FI FI914672A patent/FI914672A0/en not_active Application Discontinuation
- 1991-11-25 IN IN872MA1991 patent/IN173648B/en unknown
- 1991-11-25 IN IN871MA1991 patent/IN173647B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: LAPORTE INDUSTRIES LTD., LONDON, GB |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: LENZING GERBER PATENTANWAELTE, 40470 DUESSELDORF |
|
| 8339 | Ceased/non-payment of the annual fee |